cis(+) et cis(-) 5,6-dihydroxy-5,6-dihydrothymidine | 38709-52-3

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: cis(+) et cis(-) 5,6-dihydroxy-5,6-dihydrothymidine
• 英文别名: Thymidine, 5,6-dihydro-5,6-dihydroxy-, (5S,6R)-；(5S,6R)-5,6-dihydroxy-1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-methyl-1,3-diazinane-2,4-dione
• CAS: 38709-52-3
• 化学式: C₁₀H₁₆N₂O₇
• 分子量: 276.246
• InChiKey: RKEITGVZZHXKON-ZTOQJESFSA-N

物化性质

• 密度：
  1.645±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.4
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  140
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  cis(+) et cis(-) 5,6-dihydroxy-5,6-dihydrothymidine 生成 6-ethoxy-5-hydroxy-5-methyl-1,3-diazinane-2,4-dione
  参考文献：
  名称：

  POLVERELLI, MICHEL;BERGER, MAURICE;CADET, JEAN, NUCLEOSIDES AND NUCLEOTIDES, 10,(1991) N-3, C. 563-564

  摘要：

  DOI：
• 作为产物：
  描述：

  3,5-双-o-(t-丁基二甲基甲硅烷基)胸腺嘧啶脱氧核苷 在 四氧化锇 四丁基氟化铵 、 N-甲基吗啉氧化物 作用下， 以 四氢呋喃 、 水 、 叔丁醇 为溶剂， 反应 42.0h， 生成 cis(+) et cis(-) 5,6-dihydroxy-5,6-dihydrothymidine
  参考文献：
  名称：

  Diastereoselective synthesis of hydroxylated dihydrothymidines resulting from oxidative stress

  摘要：

  DOI：

  10.1021/jo00074a057

文献信息

• Radiation-induced binding of 2,2,6,6-tetramethyl-1,4-piperidone-<i>N</i>-oxyl to thymidine in oxygen-free aqueous solutions. Isolation and characterization of the adducts
  作者：Maurice Berger、Jean Cadet、Jacques Ulrich

  DOI：10.1139/v85-002

  日期：1985.1.1

  Steady-state γ-radiolysis of deaerated aqueous solutions of thymidine has been carried out in the presence of 2,2,6,6-tetramethyl-1,4-piperidone-N-oxyl (TAN), a well-known radiosensitizing agent. The eight main radiation-induced TAN addition products to thymidine have been isolated and characterized by 1H and 13C nmr, cd, and fast-atom bombardment mass spectrometry measurements.

  已在 2,2,6,6-四甲基-1,4-哌啶酮-N-氧基 (TAN)（一种众所周知的放射增敏剂）存在下对脱气的胸苷水溶液进行稳态 γ-辐射分解。胸苷的八种主要辐射诱导的 TAN 加成产物已被分离出来，并通过 1H 和 13C nmr、cd 和快速原子轰击质谱测量进行表征。
• Itahara, Toshio; Koga, Sunao, Chemistry Letters, 1991, # 1, p. 85 - 88
  作者：Itahara, Toshio、Koga, Sunao

  DOI：——

  日期：——
• Cadet, J.; Voituriez, L.; Berger, M., Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 12, p. 1643 - 1651
  作者：Cadet, J.、Voituriez, L.、Berger, M.、Myers, L. S., (Jr.)

  DOI：——

  日期：——
• Synthesis and Kinetic Study of the Deamination of the <i>Cis</i> Diastereomers of 5,6-Dihydroxy-5,6-dihydro-5-methyl-2‘-deoxycytidine
  作者：Carine Bienvenu、Jean Cadet

  DOI：10.1021/jo951900e

  日期：1996.1.1

  The main objectives of the present work were the synthesis of the two cis diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine and the kinetic study of their hydrolytic deamination. The preparation of the two glycols, two main (OH)-O-.-mediated oxidation products of 5-methyl-2'-deoxycytidine, was achieved in two steps. The first one involved the synthesis of the two trans-(5R,6S)- and (5S,6R)-5-bromo-6-hydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine. In a subsequent step, the bromohydrins were specifically converted into the cis-(5S,6S) and (5R,6R) diastereomers of 5,6-dihydroxy-5,6-dihydro-5-methyl-2'-deoxycytidine, respectively, under slightly alkaline conditions. The resulting glycols were purified by reverse phase high performance liquid chromatography and characterized by extensive spectroscopy measurements including C-13- and H-1-NMR analyses. Exact mass determination was Inferred from high resolution fast atom bombardment mass spectrometry measurements. Circular dichroism spectroscopy confirmed the diastereomeric relationship existing between the pair of glycols. Kinetic study of the deamination of the above glycols was carried out in phosphate buffer solutions (pH 7) at two different temperatures (37 degrees C and 25 degrees C) in order to determine the thermodynamic and kinetic parameters of the reaction.
• Boorstein, R. J.; Cadet, J.; Hilbert, T., Journal de Chimie Physique et de Physico-Chimie Biologique, 1993, vol. 90, # 4, p. 837 - 852
  作者：Boorstein, R. J.、Cadet, J.、Hilbert, T.、Lustig, M.、O'Donnell, R.、et al.

  DOI：——

  日期：——